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300+ stays

Stays in Gloucester

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Entire house in Beverly
Beaches, Gardens & Sublime Peace on Private Estate
5 guests2 bedrooms4 beds1 bath
Air conditioningWifiPoolBeachfront
Price:$73 / night
Entire house in Gloucester
Waterfront Annisquam Home, beautifully renovated
6 guests3 bedrooms4 beds1.5 baths
Self check-inAir conditioningWifiDishwasher
Price:$76 / night
SUPERHOST
Entire guest suite in Gloucester
SplashLanding Private Beach Getaway in Gloucester
2 guests1 bedroom1 bed1 bath
Air conditioningWifiBeachfrontWaterfront
Price:$65 / night
Entire apartment in Newburyport
Surrounded by Ocean Views, Private Deck, Private Suite, Jetted Tub: Luney Dunes Penthouse
2 guests1 bedroom1 bed1 bath
Self check-inAir conditioningWifiPets allowed
Price:$20 / night
SUPERHOST
Entire cottage in Gloucester
Cute Cottage with harbor views in a great location
4 guests3 bedrooms4 beds1 bath
Self check-inAir conditioningWifiWasher
Price:$199 / night
Entire bungalow in Rockport
Cozy Seaside Bungalow- Enjoy Rockport Year-Round
4 guests2 bedrooms3 beds1 bath
Self check-inAir conditioningWifiPets allowed
Price:$129 / night
SUPERHOST
Entire cabin in Rockport
The Dogtown Cabin at Applecart Farm
5 guests2 bedrooms3 beds1 bath
Air conditioningWifiPets allowedFree parking
Price:$161 / night
SUPERHOST
Entire cottage in Gloucester
Cottage In The Woods
3 guests2 bedrooms1 bed1 bath
Self check-inAir conditioningWifiPets allowed
Price:$130 / night
SUPERHOST
Entire apartment in Gloucester
Annisquam Bridge House/ Feb/ summer dates now open
4 guests2 bedrooms2 beds1 bath
Self check-inAir conditioningWifiWaterfront
Price:$150 / night
SUPERHOST
Entire house in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
6 guests2 bedrooms4 beds1 bath
Self check-inAir conditioningWifiIndoor fireplace
Price:$325 / night
SUPERHOST
Entire guesthouse in Gloucester
Annisquam Village Bunny Cottage
3 guests1 bedroom1 bed1 bath
Air conditioningWifiFree parking
Price:$150 / night
SUPERHOST
Entire house in Rockport
Carriage House on Historic Property
4 guests1 bedroom2 beds1 bath
Self check-inAir conditioningWifiHot tub
Price:$157 / night
SUPERHOST
Entire house in Gloucester
Gloucester getaway ocean escape
8 guests3 bedrooms5 beds2 baths
BreakfastAir conditioningWifiDishwasher
Price:$200 / night
SUPERHOST
Entire apartment in Rockport
Mary's By The Sea
4 guests1 bedroom1 bed1.5 baths
Air conditioningWifi
Price:$155 / night
SUPERHOST
Entire condominium in Rockport
Rockport Harborview ★ Private Deck & Free Parking!
2 guests1 bedroom1 bed1 bath
Self check-inAir conditioningWifiWaterfront
Price:$266 / night
SUPERHOST
Entire apartment in Gloucester
Welcoming Getaway Oasis!
6 guests2 bedrooms3 beds1 bath
Self check-inAir conditioningWifiIndoor fireplace
Price:$77 / night
Entire apartment in Gloucester
White Sand beach in a private enclave
4 guests1 bedroom2 beds1 bath
Air conditioningWifiFree parkingWasher
Price:$180 / night
SUPERHOST
Entire guest suite in Gloucester
PrivateBeach for 2 Adults, Gloucester MA SquishInn
2 guests1 bedroom1 bed1 bath
Air conditioningWifiBeachfrontWaterfront
Price:$199 / night
SUPERHOST
Entire apartment in Rockport
Ocean view kingsize south end studio
4 guests1 bedroom2 beds1 bath
Air conditioningWifiFree parkingKitchen
Price:$150 / night
SUPERHOST
Tiny house in Rockport
Little Red House on Bearskin Neck!
2 guestsStudio1 bed1 bath
WifiWaterfrontIndoor fireplaceKitchen
Price:$126 / night
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1 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.