Report 
 
      
Registrant:   Vanguard Massachusetts Tax-Exempt Funds — List all N-SARs

Annual Report for the 2nd-half period ended at fiscal year end:  11/30/08

Were there any Answer File errors in the Filing?  None FoundNone Found by SEC InfoNot Checked by the FilerOne or more Found by SEC Info
Was the Answer File completed by the Registrant?  Yes

Is this an Amendment to a previous Report?  No
Is this a change to a previous Report?      No
 
Registrant 
 
 1.
SEC CIK:      1070414
SEC File #:   811-09005

Telephone #:  610-669-1000
 
 2.
Address:      100 Vanguard Boulevard
              Malvern, PA  19355
 
 3.
Is this the first Form N-SAR filed by the Registrant?  No
 
 4.
Is this the final Form N-SAR filed by the Registrant?  No
 
 
Funds/Series 
↑Top of Form N-SAR 
     
                                                                               
 7.
Is the Registrant a Funds/Series (multiple portfolios) company?  No
 
Investment Adviser 
 
 8.1
Name:         The Vanguard Group, Inc.
Role:         Adviser
SEC File #:   801-11953
Location:     Malvern, PA
 
Administrator 
 
10.1
Name:         The Vanguard Group, Inc.
SEC File #:   801-11953
Location:     Malvern, PA
 
Principal Underwriter 
 
11.1
Name:         Vanguard Marketing Corp.
SEC File #:   008-21570
Location:     Malvern, PA
 
Shareholder Servicing/Transfer Agent 
 
12.1
Name:         The Vanguard Group, Inc.
SEC File #:   084-00772
Location:     Malvern, PA
 
Independent Public Accountant 
 
13.1
Name:         Pricewaterhousecoopers LLP
Location:     Philadelphia, PA
 
Affiliated Broker/Dealer 
 
14.1
Name:         Vanguard Marketing Corp.
SEC File #:   008-21570
 
Custodian 
 
15.1
Name:         U.S. Bank NA
Role:         Custodian
Location:     Philadelphia, PA

Type of custody:  Section 17(f)(1) — Bank
 
18.
Does the Registrant’s/Series’ Custodian(s) maintain some or all of the
Registrant’s/Series’ securities in a central depository or book-entry
system pursuant to Rule 17f-4?  Yes
 
Family of Investment Companies 
 
19.
Is the Registrant/Series part of a “family” of investment companies?  Yes

Total number of registered management investment companies, Series
and portfolios (excluding any Unit Investment Trusts) in the family:  156

The Identification Code of the family for Form N-SAR Filings:  VANGUARDGR
 
Brokerage Commissions Paid on Portfolio Transactions 
 
20.
The brokers who received the largest amount of gross brokerage
commissions during the period:
 
20.1
Broker:       Lehman Brothers Inc.
IRS #:        13-2518466
Commissions paid ($000s):  13
 
20.2
Broker:       J.P. Morgan Securities Inc.
IRS #:        13-3224016
Commissions paid ($000s):  3
 
21.
Total brokerage commissions paid by the Registrant during the period:
  Aggregate paid ($000s):  16
 
Portfolio Transactions with Entities Acting as Principals 
 
22.
The entities acting as principals with whom the Registrant did the
largest amount of portfolio transactions, based on total value of
principal, during the period:
 
22.1
Entity:       J.P. Morgan Securities Inc.
IRS #:        13-3224016
Registrant’s purchases ($000s):  62,748
Registrant’s sales ($000s):  57,420
 
22.2
Entity:       Vanguard Ltd.-Term Tax-Exempt Fund
IRS #:        23-2471390
Registrant’s purchases ($000s):  33,339
Registrant’s sales ($000s):  86,573
 
22.3
Entity:       Citigroup Global Markets Inc.
IRS #:        13-2919773
Registrant’s purchases ($000s):  56,351
Registrant’s sales ($000s):  50,245
 
22.4
Entity:       Vanguard Municipal Cash Management Fund
IRS #:        20-0961103
Registrant’s purchases ($000s):  52,000
Registrant’s sales ($000s):  52,360
 
22.5
Entity:       Goldman, Sachs & Co.
IRS #:        13-5108880
Registrant’s purchases ($000s):  52,049
Registrant’s sales ($000s):  36,140
 
22.6
Entity:       Wachovia Securities LLC
IRS #:        54-0796506
Registrant’s purchases ($000s):  59,777
Registrant’s sales ($000s):  6,504
 
22.7
Entity:       Vanguard Intermediate-Term Tax Exempt Fund
IRS #:        23-2471389
Registrant’s purchases ($000s):  20,400
Registrant’s sales ($000s):  44,365
 
22.8
Entity:       Lehman Brothers Inc.
IRS #:        13-2518466
Registrant’s purchases ($000s):  39,407
Registrant’s sales ($000s):  19,350
 
22.9
Entity:       Vanguard Tax-Exempt Money Market Fund
IRS #:        23-2471394
Registrant’s purchases ($000s):  27,800
Registrant’s sales ($000s):  18,900
 
22.10
Entity:       RBC Dain Rauscher Inc.
IRS #:        41-0212020
Registrant’s purchases ($000s):  15,998
Registrant’s sales ($000s):  29,829
 
23.
Total purchase/sale transactions by the Registrant during the period:
   Aggregate purchases ($000s):  608,245
   Aggregate sales ($000s):  509,142
 
Holdings of Securities Issued by Registrant’s/Series’ Brokers or Dealers 
 
24.
At period end, did the Registrant/Series hold any securities of the
Registrant’s/Series’ regular brokers or dealers, or of the parents of
such brokers or dealers, that derive more than 15% of gross revenue from
securities-related activities?  No
 
Considerations which Affected the Participation of Brokers or Dealers 
 
26.
Considerations which affected the participation of brokers or dealers or
other entities in commissions or other compensation paid on portfolio
transactions of the Registrant:

Consideration?
Sales of the Registrant’s/Series’ shares ...............................  No
Receipt of investment research and statistical info ....................  Yes
Receipt of quotations for portfolio valuations .........................  No
Ability to execute portfolio transactions to obtain the best price
  and execution ........................................................  Yes
Receipt of telephone line and wire services ............................  No
Broker or Dealer which is an affiliated person .........................  No
An arrangement to return or credit part or all of commissions or
  profits thereon...
    To an Investment Adviser or Principal Underwriter, or to an
      affiliated person of either ......................................  No
    To the Registrant ..................................................  Yes
Other ..................................................................  No
 
Investment Company Type 
 
27.
Is the Registrant an “open-end” investment company?  Yes, Open-End
 
Sales and Repurchases 
 
28.
Monthly total Net Asset Value (NAV) of sales and repurchases of the
Registrant’s/Series’ shares:
 
1st Month of period:  ($000s)
    Total NAV of shares sold:
      New sales (including exchanges) ............................
 26,554
      Reinvestment of dividends and distributions ................
 1,924
      Other ......................................................
 –
    Total NAV of shares redeemed & repurchased (inc. exchanges) ..
 10,410
2nd Month:
    Total NAV of shares sold:
      New sales (including exchanges) ............................
 19,003
      Reinvestment of dividends and distributions ................
 2,048
      Other ......................................................
 –
    Total NAV of shares redeemed & repurchased (inc. exchanges) ..
 13,644
3rd Month:
    Total NAV of shares sold:
      New sales (including exchanges) ............................
 14,517
      Reinvestment of dividends and distributions ................
 2,066
      Other ......................................................
 –
    Total NAV of shares redeemed & repurchased (inc. exchanges) ..
 6,443
4th Month:
    Total NAV of shares sold:
      New sales (including exchanges) ............................
 18,877
      Reinvestment of dividends and distributions ................
 2,051
      Other ......................................................
 –
    Total NAV of shares redeemed & repurchased (inc. exchanges) ..
 29,059
5th Month:
    Total NAV of shares sold:
      New sales (including exchanges) ............................
 22,562
      Reinvestment of dividends and distributions ................
 2,024
      Other ......................................................
 –
    Total NAV of shares redeemed & repurchased (inc. exchanges) ..
 60,081
6th Month:
    Total NAV of shares sold:
      New sales (including exchanges) ............................
 22,694
      Reinvestment of dividends and distributions ................
 1,901
      Other ......................................................
 –
    Total NAV of shares redeemed & repurchased (inc. exchanges) ..
 17,059

Total of all months:  ($000s)
    Total NAV of shares sold:
      New sales (including exchanges) ............................
 124,207
      Reinvestment of dividends and distributions ................
 12,014
      Other ......................................................
 –
    Total NAV of shares redeemed & repurchased (inc. exchanges) ..
 136,696

Total NAV of the Registrant’s/Series’ share sales during the period
subject to a sales load ($000s):  0
 
Sales Load (Front-End or Deferred) and Fees (Redemption or Maintenance) 
 
29.
Was a front-end sales load deducted from any share sales during the
period?  No
 
34.
Did the Registrant/Series impose a deferred or contingent deferred sales
load during the period?  No
 
37.
Did the Registrant/Series impose a redemption fee other than a deferred
or contingent sales load during the period?  No
 
39.
Were any account maintenance fees or other administrative fees imposed
directly on shareholders during the period?  Yes
 
Payment Plan for the Distribution of Fund Shares 
 
40.
During the period, did the Registrant/Series have a plan of distribution
adopted pursuant to Rule 12b-1?  No
 
Advisory Fee 
 
45.
Did the Registrant/Series have an advisory contract during the period?  No
 
Miscellaneous Info 
 
55.
Did the Registrant/Series have any of the following outstanding at any
time during the period which exceeded 1% of aggregate net assets:
    Overdrafts?  No
    Bank loans?  No
 
56.
During the period, did the Registrant’s/Series’ Investment Adviser(s)
have advisory clients other than investment companies?  Yes
 
57.
Did the Registrant/Series adjust the number of its shares outstanding by
means of a stock split or stock dividend?  No
 
Classification and Asset Allocation 
 
58.
Is the Registrant/Series a Separate Account of an insurance company?  No
 
59.
Is the Registrant/Series a management investment company?  Yes
 
60.
Was the Registrant/Series a diversified investment company at any time
during the period?  No

Was the Registrant/Series a diversified investment company at the end of
the period?  No
 
61.
The lowest minimum initial investment required by the Registrant/Series
from an investor that is not an employee or otherwise affiliated with
the Registrant/Series, its Investment Adviser, Principal Underwriter or
other affiliated entity:  $3,000
 
62.
Does the Registrant/Series invest primarily in debt securities,
including convertible debt securities, options & futures on debt
securities or indices of debt securities?  Yes

The percentage of net assets in each type at period end:

Debt — Short-Term Maturities
U.S. Treasury ...............................      0.0%
U.S. Government Agency ......................      0.0
Repurchase agreements .......................      0.0
State and Municipal – tax-free ..............      5.7
Bank certificates of deposit – domestic .....      0.0
Bank certificates of deposit – foreign ......      0.0
Bankers acceptances .........................      0.0
Commercial paper – taxable ..................      0.0
Time deposits ...............................      0.0
Options .....................................      0.0
All other ...................................      0.0

Debt — Intermediate & Long-Term Maturities
U.S. Treasury ...............................      0.0%
U.S. Government Agency ......................      0.0
State and Municipal – tax-free ..............    93.2
Corporate ...................................      0.0
All other ...................................      0.0

Non-Debt
Investments other than debt securities ......      0.0%
 
63.
The dollar-weighted average portfolio maturity at period end in days or,
if longer than one year, in years (to one decimal place):
    Days:     0
    Years:    11.1
 
64.
Is the timely payment of principal and interest on any of the
instruments listed in Item 62 insured or guaranteed by an entity other
than the issuer?  Yes

Is the issuer of any instrument covered in Item 62 delinquent or in
default as to payment of principal or interest at period end?  No
 
66.
Is the Registrant/Series a Fund that usually invests in equity
securities, options & futures on equity securities, indices of equity
securities or securities convertible into equity securities?  No
 
67.
Is the Registrant/Series a “balanced” Fund?  No
 
68.
Does the Registrant/Series have more than 50% of its net assets at
period end invested in the securities of issuers...
    Engaged primarily in production or distribution of precious metals?  No
    Located primarily in countries other than the United States?  No
 
69.
Is the Registrant/Series an index Fund?  No
 
Investment Practices 
 
70.
Activities that are permitted by the Registrant’s/Series’ investment
policies, and which were engaged in during the period:

Activity                                            Permitted Engaged In
Writing or investing in repurchase agreements?           Yes      No
Writing or investing in options on equities?             No        –
Writing or investing in options on debt securities?      Yes      No
Writing or investing in options on stock indices?        No        –
Writing or investing in interest rate futures?           Yes to both
Writing or investing in stock index futures?             No        –
Writing or investing in options on futures?              Yes      No
Writing or investing in options on stock index futures?  No        –
Writing or investing in other commodity futures?         No        –
Investments in restricted securities?                    Yes to both
Investments in shares of other investment companies?     Yes to both
Investments in securities of foreign issuers?            No        –
Currency exchange transactions?                          No        –
Loaning portfolio securities?                            Yes      No
Borrowing of money?                                      Yes      No
Purchases/sales by certain exempted affiliated persons?  Yes to both
Margin purchases?                                        No        –
Short selling?                                           No        –
 
Portfolio Turnover 
 
71.
Portfolio turnover rate for the period:
 
Purchases ($000s):  290,917
Sales ($000s):      205,672

Monthly average Value of portfolio ($000s):  698,085

Percent turnover (lesser of Purchases or Sales, divided by Value):  29%
 
Financial Info — Income and Expenses 
 
72.
The number of months covered by the values in Items 72 and 73:  12

Income  ($000s)
Net interest income ..............................................
 31,600
Net dividend income ..............................................
 –
Account maintenance fees .........................................
 –
Net other income .................................................
 –

Expenses  ($000s)
Advisory fees ....................................................
 70
Administrator fees ...............................................
 382
Salaries and other compensation ..................................
 –
Shareholder Servicing Agent fees .................................
 226
Custodian fees ...................................................
 7
Postage ..........................................................
 –
Printing expenses ................................................
 7
Directors’ fees ..................................................
 1
Registration fees ................................................
 –
Taxes ............................................................
 –
Interest .........................................................
 –
Bookkeeping fees paid to anyone performing this service ..........
 –
Auditing fees ....................................................
 23
Legal fees .......................................................
 –
Marketing/distribution payments, incl. Rule 12b-1 plan payments ..
 193
Amortization of organization expenses ............................
 –
Shareholder meeting expenses .....................................
 –
Other expenses ...................................................
 –
Total expenses ...................................................
 909

Expense reimbursements ($000s):   5

Net investment income ($000s):    30,696

Realized capital gains ($000s):   3,299
Realized capital losses ($000s):  9,725

Net unrealized appreciation during the period ($000s):  0
Net unrealized depreciation during the period ($000s):  46,719

Total income dividends for which the record date passed during the
period ($000s):  30,696

Total capital gains distributions for which the record date passed
during the period ($000s):  0
 
73.
Distributions per share for which the record date passed during the
period, shown in fractions of a cent, if so declared:

Dividends from net investment income:    $0.4140

Distribution of capital gains:  $0.0000
Other distributions:            $0.0000
 
Financial Info — Condensed Balance Sheet Data 
 
74.
Assets  ($000s)
Cash .............................................................
 6
Repurchase agreements ............................................
 –
Short-term debt securities, other than repurchase agreements .....
 40,794
Long-term debt securities, including convertible debt ............
 661,596
Preferred, conv. preferred and adjustable-rate preferred stock ...
 –
Common stock .....................................................
 –
Options on equities ..............................................
 –
Options on all futures ...........................................
 –
Other investments ................................................
 73
Receivables from portfolio instruments sold ......................
 30
Receivables from affiliated persons ..............................
 –
Other receivables ................................................
 11,471
All other assets .................................................
 –
Total assets .....................................................
 713,970

Liabilities  ($000s)
Payables for portfolio instruments purchased .....................
 –
Amounts owed to affiliated persons ...............................
 885
Senior long-term debt ............................................
 –
Other liabilities:
  Reverse repurchase agreements ..................................
 –
  Short sales ....................................................
 –
  Written options ................................................
 –
  All other liabilities ..........................................
 2,815

Equity  ($000s)
Senior equity ....................................................
 –
Net assets of common shareholders ................................
 710,270

Number of shares outstanding (000s):   75,232

Net Asset Value (NAV) per share (to nearest cent):  $9.44

Total number of shareholder accounts:  4,785

Total value of assets in segregated accounts ($000s):  1,512
 
75.
Monthly average net assets during the period ($000s):  730,806
 
Additional Disclosures 
 
77.
Did the Registrant file any additional Exhibits with the filing of this
Report (listed here and filed either herewith — as one of the ‘EX-99.*’
↑Exhibits in this Filing — or separately and incorporated by reference)?  Yes

EX-99.77B:  Accountant’s Report re: Internal Controls?  Yes

EX-99.77Q1: Other Disclosure?  Yes

EX-99.77Q3: Other Info?  Yes
 
Subsidiaries 
 
78.
Does the Registrant have any wholly-owned investment company
subsidiaries whose operating and financial data are consolidated with
that of the Registrant in this Report?  No
 
Fidelity Bond in Effect at Fiscal Year End 
 
80.
Insurer:      ICI Mutual Insurance Co.
2nd Insurer:  N/A

Aggregate face amount of coverage for the Registrant/Series on all bonds
on which it is named as an insured ($000s):  400,000
 
81.
Is the bond part of a joint fidelity bond(s) shared with other
investment companies or other entities?  Yes

How many other investment companies or other entities are covered by the
bond (counting each Fund/Series as a separate investment company):  206
 
82.
Does the mandatory coverage of the fidelity bond have a deductible?  No
 
83.
Were any claims with respect to this Registrant/Series filed under the
bond during the period?  No
 
84.
Were any losses incurred with respect to this Registrant/Series that
could have been filed as a claim under the fidelity bond but were not?  No
 
85.
Are the Registrant’s/Series’ Officers and Directors covered as Officers
and Directors of the Registrant/Series under any errors and omissions
insurance policy owned by the Registrant/Series or anyone else?  Yes

Were any claims filed under such policy during the period with respect
to the Registrant/Series?  No
 
 Signature 
 
↑Top of Form N-SAR 
     
                                                                               
/s/      William Gessig      
Name:   William Gessig
Title:  Manager