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591 Houses

15

Stunning Studio in Woods

Massachusetts / Wenham

Wenham apartment

1 2 30 nights min

  • 1 bedroom
  • sleeps 2
  • 30 nights min
  • Beach / lakeside relaxation
  • Air conditioning

Price per night from

$75

Responds fast!
avg. 3 hours 12 minutes

Price per night from

$75

Great rentals within 20 miles that match your search

Distance approx 19.27 km from Wenham

(6) Excellent 

20

Charming 4 room apartment, minutes from Cambridge and Boston

Massachusetts / Arlington

Arlington apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$174

Responds fast!
avg. 50 minutes

Price per night from

$174

Distance approx 19.06 km from Wenham

(1) Excellent 

22

Historic, elegant duplex in Beacon Hill in the heart of Boston two bedrooms

Massachusetts / Boston

Boston apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning

Price per night from

$305

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$305

Distance approx 16.3 km from Wenham

4

Queen One Bedroom Suite

Massachusetts / Winthrop

Winthrop hotel apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$259

Price per night from

$259

Distance approx 7.96 km from Wenham Show on Map

17

Family Paradise on Peaceful Cove. Private Island

Massachusetts / Ipswich

Ipswich house

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 0.1 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$249

Price per night from

$249

Distance approx 8.03 km from Wenham Show on Map

(1) Excellent 

40

Hillside Ocean View 2BR with Private Beach Access

Massachusetts / Ipswich

Ipswich house

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$150

Responds fast!
avg. 3 hours 12 minutes

Price per night from

$150

Distance approx 14.66 km from Wenham

25

2017 Rental Plum Island Waterfront home Newbury Ma

Massachusetts / Newbury

Newbury house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 0.25 mi
  • Child Friendly
  • Air conditioning

Price per night from

$711

Price per night from

$711

Distance approx 15.11 km from Wenham

18

GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN

Cape Ann / Rockport

Rockport apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$213

Responds fast!
avg. 37 minutes

Price per night from

$213

Distance approx 13.21 km from Wenham

39

Stunning Views - Spacious Home

Cape Ann / Gloucester

Gloucester house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi

Price per night from

$498

Price per night from

$498

Distance approx 13.23 km from Wenham

17

Beachside at Good Harbor

Cape Ann / Gloucester

Gloucester house

5 13 2 nights min

  • 5 bedrooms
  • sleeps 13
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.32 mi
  • Child Friendly

Price per night from

$427

Price per night from

$427

Distance approx 12.1 km from Wenham

7

Fabulous Waterfront 2 Bedroom - Boat dock option

Cape Ann / Gloucester

Gloucester apartment

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about pets

Price per night from

$67

Price per night from

$67

Distance approx 7.6 km from Wenham Show on Map

(48) Excellent 

Certificate of Excellence

25

ChestnutSweet, for a sweet New England get-away!

Massachusetts / Marblehead

Marblehead apartment

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi
  • Air conditioning
“The home and stay were wonderful - perfectly wonderful!” The rental home is amazing. The home is decorated so tastefully, and it is filled with very quality furnishings and linens. We felt that the home was quite spacious and the layout worked very
…see more

Certificate of Excellence

Price per night from

$175

Price per night from

$175

Distance approx 18.86 km from Wenham

(1) Excellent 

12

New, Super Cool 2 bedroom steps to Fanuile Hall

Massachusetts / Boston

Boston apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning
“Perfect location, great space, great service, and would stay there again.” The rental agent, Elyne, could not have been more helpful from beginning to end. She is responsive and trustworthy. My husband left his prescription eyeglasses in the apartmen
…see more

Price per night from

$279

Price per night from

$279

Distance approx 15.14 km from Wenham

(2) Excellent 

18

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Cape Ann / Rockport

Rockport cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Child Friendly

Price per night from

$188

Responds fast!
avg. 37 minutes

Price per night from

$188

Distance approx 18.86 km from Wenham

10

Beautiful, new, one bedroom, amazing location

Massachusetts / Boston

Boston apartment

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$174

Price per night from

$174

Distance approx 6.56 km from Wenham Show on Map

17

The Cottage

Cape Ann / Manchester-by-the-Sea

Manchester-by-the-Sea house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.25 mi
  • Child Friendly
  • Private garden

Price per night from

$391

Price per night from

$391

Distance approx 6.14 km from Wenham Show on Map

7

New England Room+Bkft (SW)

Massachusetts / Ipswich

Ipswich b and b

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Air conditioning
  • Pet Friendly

Price per night from

$177

Responds fast!
avg. 3 hours 12 minutes

Price per night from

$177

Distance approx 13.98 km from Wenham

(1) Excellent 

17

Back Beach Cottages - Charming house & guest house

Cape Ann / Rockport

Rockport house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 0.1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$453

Price per night from

$453

Distance approx 19.12 km from Wenham

16

Close 2T Private Room with AirBed

Massachusetts / Boston

Boston apartment

1 1 30 nights min

  • 1 bedroom
  • sleeps 1
  • 30 nights min

Price per night from

$36

Responds fast!
avg. 3 hours 37 minutes

Price per night from

$36

Distance approx 14.38 km from Wenham

(1) Very Good 

15

A Year-Round Vacation Home

Cape Ann / Rockport

Rockport house

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$249

Responds fast!
avg. 3 hours 31 minutes

Price per night from

$249

Distance approx 19.8 km from Wenham

5

Cambridge Trip Decker

Massachusetts / Cambridge

Cambridge apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly

Price per night from

$995

Price per night from

$995

Distance approx 6.75 km from Wenham Show on Map

4

Booth Cottage

Cape Ann / Manchester-by-the-Sea

Manchester-by-the-Sea house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$895

Price per night from

$895

Distance approx 14.88 km from Wenham

8

1 minute walk to subway, 10 minutes to airport

Massachusetts / Revere

Revere b and b

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$70

Responds fast!
avg. 3 hours 24 minutes

Price per night from

$70

Distance approx 5.85 km from Wenham Show on Map

13

Loft Apartment A at Cedar Hill Farm B&B

Cape Ann / Essex

Essex apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Air conditioning

Price per night from

$174

Price per night from

$174

Distance approx 14.01 km from Wenham

(35) Excellent 

Certificate of Excellence

23

Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet

Cape Ann / Rockport

Rockport cottage

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 mi
  • Car not necessary
“It was very peaceful and welcoming.” Forgot your toothbrush? Don't worry, there's one there. Forgot your shaving cream? Again, not to worry. Rosemarie provided all that was needed and more. We prefer to cook our own breakfast and found that all th
…see more

Certificate of Excellence

Price per night from

$125

Price per night from

$125

Distance approx 17.73 km from Wenham

4

Room in Huge Modern, 4BR Condo (2)

Massachusetts / Somerville

Somerville room

1 1 30 nights min

  • 1 bedroom
  • sleeps 1
  • 30 nights min
  • Ask about pets

Price per night from

$60

Price per night from

$60

Distance approx 15.04 km from Wenham

11

Beautiful

Massachusetts / Malden

Malden house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$350

Responds fast!
avg. 30 minutes

Price per night from

$350

Distance approx 11.7 km from Wenham

23

Relax at Rocky Neck Hideaway

Cape Ann / Gloucester

Gloucester townhouse

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$129

Price per night from

$129

Distance approx 17.83 km from Wenham

1

4 BR Medford Square

Massachusetts / Medford

Medford house

4 4 1 night min

  • 4 bedrooms
  • sleeps 4
  • 1 night min

Price per night from

$498

Price per night from

$498

Distance approx 11.47 km from Wenham

4

Test Property- TA Test

Cape Ann / Gloucester

Gloucester cottage

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$12

Price per night from

$12

Distance approx 19.25 km from Wenham

(2)  

9

Boston Harbor View 1 Bedroom Luxury Suites

Massachusetts / Boston

Boston apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$125

Price per night from

$125

Distance approx 17.74 km from Wenham

6

Nice room in Charlestown

Massachusetts / Boston

Boston condo

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min

Price per night from

$70

Price per night from

$70

Distance approx 10.04 km from Wenham

9

Large Furnished room for rent, quiet location

Massachusetts / Lynn

Lynn apartment

1 1 90 nights min

  • 1 bedroom
  • sleeps 1
  • 90 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$25

Price per night from

$25

Distance approx 15.11 km from Wenham

17

OCEAN VIEW COTTAGE AT THE SEAWARD - EASY SEASIDE PATH TO OLD GARDEN BEACH

Cape Ann / Rockport

Rockport cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$223

Responds fast!
avg. 37 minutes

Price per night from

$223

Distance approx 19.12 km from Wenham

(42) Excellent 

Certificate of Excellence

10

Beacon Hill -- "Luci Bella" elegant one bedroom

Massachusetts / Boston

Boston apartment

1 3 30 nights min

  • 1 bedroom
  • sleeps 3
  • 30 nights min
  • Car not necessary
  • Air conditioning
“Seriously fantastic!” We would sincerely like to thank owner Paul. This was a truly great holiday. I lived in Boston some time ago and had managed to obtain some cheap flights back for a weeks vacation with my partner. This apartment was the perfect w
…see more

Certificate of Excellence

Price per night from

$108

Responds fast!
avg. 3 hours 24 minutes

Price per night from

$108

Distance approx 18.94 km from Wenham

7

Spacious 3 bedroom near everything

Massachusetts / Boston

Boston apartment

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$194

Price per night from

$194

Distance approx 18.56 km from Wenham

(22) Excellent 

29

Boston North End luxury apartment.

Massachusetts / Boston

Boston apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Ask about children
  • Car not necessary
  • Air conditioning
“Perfect North End Rental” We loved this super clean one bedroom in the heart of the North End of Boston. Furniture, decor and amenities made us feel right at home. Bonus: we were within walking distance of everything wonderful about Boston i.e. highl
…see more

Price per night from

$229

Price per night from

$229

Distance approx 14.16 km from Wenham

(4) Excellent 

46

Directly on Long Beach Rockport MA

Cape Ann / Rockport

Rockport house

4 14 7 nights min

  • 4 bedrooms
  • sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$578

Price per night from

$578